540 Monticello St · Winchester, VA 22601

$605,000

9 bd · 3.9 ba · 4,396 sqft · MultiFamily public records · 122 Days on market

Built 1956 Good condition 3,999 sqft lot

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Why this score? — see what drove the D+ grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +15.5/30.0
• ARV discount +7.5/15.0
• DSCR +4.8/10.0
• Schools +4.8/10.0
• Condition / age +3.8/5.0
• Livability +3.7/5.0
• Rent growth +3.4/5.0
• 1% rule +3.3/10.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 3 units. estimate disagrees with records

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks MLS

Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit The roof less than 3 years old New HVAC installed (2025) Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $45,300. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!

Key facts

• Large kitchens
• Updated finishes
• Ground level unit

Tags

• TRIPLEX IN DOWNTOWN WINCHESTER
• LARGE KITCHENS
• UPDATED FINISHES
• LAUNDRY ROOMS
• GROUND LEVEL UNIT
• 2ND-LEVEL UNIT

What this means for you Summary

Snapshot

• This is a 2×2bd/1ba + 1×3bd/1ba units multifamily listed at $605k. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $248 ($3k/yr) — positive. Per door: $83/mo.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $504k (16.8% below list).
• Recommended offer: $504k (16.8% below list) — sets the bar for 1% rule.
• Cap rate 6.8% vs local median 3.1% in Winchester — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 74/100 on livability (#138 in VA, #4,429 nationally) — a middle-class / working-renter tenant base. Strengths: housing A+, health & safety A+, schools A-; Watch: commute F.
• Winchester City Public School District (urban): math 52% / reading 62% proficiency, ranked #73 of 131 in VA (top 56%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents rising (+3.6%/yr); 144 active listings in the ZIP; 91 units permitted in Winchester city in 2024 (52 in 5+ unit buildings).
• At $5,036/mo this rent would consume 94% of the median local household income ($64k/yr) (locally 1627% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $18k of value loss. Plan a longer hold.
• Winchester County population projected at +15% by 2050 — modest demand growth; plan on rents tracking national, not racing it.

Negotiation context

• It's been on market 122 days — a 12% lower offer ($532k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 2y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.

Risks & watch-outs

• Watch-outs: built in 1956 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $503,600 (16.8% below list)

Questions for the listing agent

1. It's been on market 122 days. Have you received any prior offers? Is the seller open to a 17% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1956 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
8. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
9. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
10. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
11. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 0.83% ✗
• Cap rate: 6.78%
• Cash-on-cash: 1.76%
• DSCR: 1.08
• GRM: 10.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 3.58% rent growth · sell at horizon

5-year hold

• IRR: -13.0%
• Equity multiple: 0.53×
• Total profit: $-79,495
• Equity at exit: $90,207

10-year hold

• IRR: -3.2%
• Equity multiple: 0.78×
• Total profit: $-37,438
• Equity at exit: $52,309

Cash invested: $169,400 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 55 Moderately Landlord-Leaning
• State Virginia: 55 Moderately Landlord-Leaning · D+2
• County: — inherits STATE
• City: — inherits STATE

VRLTA gives some tenant protections; Northern Virginia courts slower; rural VA landlord-leaning.

Methodology + full state rankings →

ZIP-level market 22601

• Rents YoY: 3.6%
• Active inventory: 144
• Price-to-rent: 31.2×

Monthly cashflow live

• Estimated rent: $5,036 high
• Mortgage (P&I): −$3,173
• Tax from tax record: −$306 /mo · $3,670/yr
• Insurance: −$252
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,058
• Net cashflow: $248

Break-even live

Break-even rent $4,722

Max offer price $605,000

Occupancy floor 90%

Sensitivity live

Price	-10% $590	-5% $419	+0% $248	+5% $77	+10% $-95
Rent	-10% $-150	-5% $49	+0% $248	+5% $447	+10% $646
Rate	-1.0pp $553	-0.5pp $402	base $248	+0.5pp $91	+1.0pp $-68

3-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$3,236
1× unit	3	1	$1,800
Total (3 units)			$5,036

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $151,250
• Closing costs: $18,150
• Reserves months: —
• Total cash needed: —

Listing history 29 events

1. 2026-06-19
   days on market $605,000 Active 122 DOM
2. 2026-06-18
   days on market $605,000 Active 121 DOM
3. 2026-06-17
   days on market $605,000 Active 120 DOM
4. 2026-06-16
   days on market $605,000 Active 119 DOM
5. 2026-06-15
   days on market $605,000 Active 118 DOM
6. 2026-06-14
   days on market $605,000 Active 116 DOM
7. 2026-06-13
   days on market $605,000 Active 115 DOM
8. 2026-06-10
   days on market $605,000 Active 113 DOM
9. 2026-06-09
   days on market $605,000 Active 112 DOM
10. 2026-06-08
    days on market $605,000 Active 111 DOM
11. 2026-06-07
    days on market $605,000 Active 110 DOM
12. 2026-06-05
    days on market $605,000 Active 107 DOM
13. 2026-06-03
    days on market $605,000 Active 106 DOM
14. 2026-06-02
    days on market $605,000 Active 105 DOM
15. 2026-06-01
    days on market $605,000 Active 104 DOM
16. 2026-05-31
    days on market $605,000 Active 103 DOM
17. 2026-05-30
    days on market $605,000 Active 102 DOM
18. 2026-02-17
    listed $605,000 Active 1647-char remark

    Show marketing remark (1647 chars)

    Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit The roof less than 3 years old New HVAC installed (2025) Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $45,300. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!

19. 2026-01-03
    historical
20. 2025-10-24
    listed $605,000 Active
21. 2025-10-21
    historical
22. 2025-07-25
    price $615,000
23. 2025-04-23
    listed $625,000 Active
24. 2025-01-31
    historical
25. 2025-01-07
    price $579,900
26. 2025-01-04
    price $579,925
27. 2024-12-06
    price $579,950
28. 2024-12-05
    price $579,975
29. 2024-09-08
    listed $580,000 Active

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast VA · Resets to sale price

• Current annual tax: $3,670 · $306/mo
• Projected year-2 tax: $4,961 · $413/mo
• Expected delta: +$1,291/yr (+$108/mo · 35.2%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 2/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥101°F today · 15 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 100% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $60,432
• − Mortgage interest: −$33,889
• − Property taxes: −$3,670
• − Insurance: −$3,025
• − Repairs & maintenance: −$4,835
• − Management: −$4,835
• − Depreciation: −$17,600
• Taxable loss: −$7,421
• Est. tax savings @ 24.0%: +$1,781
• After-tax cash flow: $4,755/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Condition & rehab AI · 12 photos

Good 75/100 Cosmetic rehab

A well-maintained triplex in a prime location, ready for a fresh coat of paint and some decluttering to maximize its value.

Value-add opportunities

• Both Painting and decluttering — Enhances curb appeal and interior aesthetics
• Both Landscaping improvements — Enhances curb appeal and property value
• Both Kitchen organization — Improves functionality and aesthetics

Renovation cost estimate screening

Value-add ROI direction

• Both Painting and decluttering — Enhances curb appeal and interior aesthetics ↑
• Both Landscaping improvements — Enhances curb appeal and property value ↑
• Both Kitchen organization — Improves functionality and aesthetics ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Winchester City Public School District
• NCES district ID: 5104050
• Math proficiency: 52% ▼ -25.00%
• Reading proficiency: 62% ▼ -5.00%
• Median HH income: $46,544
• Composite: 48.23/100
• National rank: #2164
• State rank: #73 of 131 in VA

Livability — Winchester

• Score: 74/100
• State rank: #138
• US rank: #4429

Category grades

Amenities B Commute F Cost of living B Crime C Employment C+ Housing A+ Health & safety A+ User ratings F

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winchester, VA
• County: Winchester City · 29,230 people
• City population: 62,070
• Metro: Winchester, VA-WV
• Population (ZIP): 29,230
• Household income: $64,258
• Rent vs Own: 56.2% rent · 43.8% own
• Severe rent burden: 1627.0

Population outlook (Winchester County) Hauer SSP2

• Today (2025): 29,693 people
• By 2030: 30,745 · +3.5%
• By 2040: 32,619 · +9.9%
• By 2050: 34,014 · +14.6%
• By 2075: 35,490 · +19.5%
• By 2100: 35,424 · +19.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.56)
• Race & ethnicity: White 63% Hispanic / Latino 19% Two or more races 11% Black 10% Asian 2%
• Hispanic origin (detail): Mexican 7%
• Common ancestry: Italian 3% Romanian 2% Lithuanian 2%
• Foreign-born: 12% · Canada
• Languages at home: 80% English-only · Spanish 15% French/Haitian/Cajun 1% Other Indo-European 1%

Political lean MEDSL · Winchester

• 2024 margin: Lean D (+9.8) · D 54.2% · R 44.4% · Other 1.4%
• 2008→2024 swing: +4.4pp toward D · 2008: 5.4pp · 2024: 9.8pp
• All cycles: 2024: D+9.8 2020: D+11.5 2016: D+3.5 2012: D+1.4 2008: D+5.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -245.80%
• Current HPI: 297.2882
• Rent YoY: ▲ 3.58%
• Metro: Winchester, VA-WV
• State GDP YoY: ▲ 2.40%
• F500 in state: 50

Industry mix (Fortune 500 HQ in VA)

Industry	F500 HQs	Revenue
▸Aerospace / Defense	4	$236B
▸Technology / Defense	3	$32B
▸Financial Services	2	$176B
▸Utilities	2	$27B
▸Insurance	2	$25B
▸Technology	2	$15B

Price history

+4.3% since first listed

12 events — show timeline

• 2026-02-17 Listed $605,000 BRIGHT MLS
• 2026-01-03 Listing Removed — BRIGHT MLS
• 2025-10-24 Listed $605,000 BRIGHT MLS
• 2025-10-21 Listing Removed — BRIGHT MLS
• 2025-07-25 Price Changed $615,000 BRIGHT MLS
• 2025-04-23 Listed $625,000 BRIGHT MLS
• 2025-01-31 Listing Removed — BRIGHT MLS
• 2025-01-07 Price Changed $579,900 BRIGHT MLS
• 2025-01-04 Price Changed $579,925 BRIGHT MLS
• 2024-12-06 Price Changed $579,950 BRIGHT MLS
• 2024-12-05 Price Changed $579,975 BRIGHT MLS
• 2024-09-08 Listed $580,000 BRIGHT MLS

Property tax history

+8.5%/yr

Latest (2025): $3,670 · +17.8% YoY. Source: county tax records.